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Diselenolane-Mediated Cellular Uptake: Efficient Cytosolic Delivery of Probes, Peptides, Proteins, Artificial Metalloenzymes and Protein-Coated Quantum Dots.

  • Bartolami E National Centre of Competence in Research (NCCR) Chemical Biology, School of Chemistry and Biochemistry, University of Geneva, CH-1211, Geneva, Switzerland.
  • Basagiannis D National Centre of Competence in Research (NCCR) Chemical Biology, School of Chemistry and Biochemistry, University of Geneva, CH-1211, Geneva, Switzerland.
  • Zong L National Centre of Competence in Research (NCCR) Chemical Biology, School of Chemistry and Biochemistry, University of Geneva, CH-1211, Geneva, Switzerland.
  • Martinent R National Centre of Competence in Research (NCCR) Chemical Biology, School of Chemistry and Biochemistry, University of Geneva, CH-1211, Geneva, Switzerland.
  • Okamoto Y Department of Chemistry, University of Basel, Basel, Switzerland.
  • Laurent Q National Centre of Competence in Research (NCCR) Chemical Biology, School of Chemistry and Biochemistry, University of Geneva, CH-1211, Geneva, Switzerland.
  • Ward TR Department of Chemistry, University of Basel, Basel, Switzerland.
  • Gonzalez-Gaitan M National Centre of Competence in Research (NCCR) Chemical Biology, School of Chemistry and Biochemistry, University of Geneva, CH-1211, Geneva, Switzerland.
  • Sakai N National Centre of Competence in Research (NCCR) Chemical Biology, School of Chemistry and Biochemistry, University of Geneva, CH-1211, Geneva, Switzerland.
  • Matile S National Centre of Competence in Research (NCCR) Chemical Biology, School of Chemistry and Biochemistry, University of Geneva, CH-1211, Geneva, Switzerland.
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  • 2019-03-01
Published in:
  • Chemistry (Weinheim an der Bergstrasse, Germany). - 2019
biotechnology
diselenolane
protein delivery
ring tension
streptavidin
Actins
Amino Acid Sequence
Biological Transport
Cell Line
Cell-Penetrating Peptides
Cytosol
Diffusion
Fluorescent Dyes
Metalloproteins
Models, Molecular
Optical Imaging
Phalloidine
Quantum Dots
Selenium Compounds
English Cyclic oligochalcogenides are emerging as powerful tools to penetrate cells. With disulfide ring tension maximized, selenium chemistry had to be explored next to enhance speed and selectivity of dynamic covalent exchange on the way into the cytosol. We show that diseleno lipoic acid (DiSeL) delivers a variety of relevant substrates. DiSeL-driven uptake of artificial metalloenzymes enables bioorthogonal fluorophore uncaging within cells. Binding of a bicyclic peptide, phalloidin, to actin fibers evinces targeted delivery to the cytosol. Automated tracking of diffusive compared to directed motility and immobility localizes 79 % of protein-coated quantum dots (QDs) in the cytosol, with little endosomal capture (0.06 %). These results suggest that diselenolanes might act as molecular walkers along disulfide tracks in locally denatured membrane proteins, surrounded by adaptive micellar membrane defects. Miniscule and versatile, DiSeL tags are also readily available, stable, soluble, and non-toxic.
Language
  • English
Open access status
green
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Persistent URL
https://sonar.ch/global/documents/242818
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